Sodium Hydroxide → 2-phenyl-1H-indol-3-amine

HRID 967732Notes

Reaction equation

HRID 967732 reaction equation
[N:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.[OH-].[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>C(O)C>[NH2:1][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24489Sodium DithioniteHCID 3439763-Nitroso-2-phenyl-1H-indole

Product 1

HCID 27493402-phenyl-1H-indol-3-amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 3-nitroso-2-phenyl indole (28) (25 gm, 0.129 mol) in ethanol (450 ml) was added 2N sodium hydroxide (300 mL, 5.0 eq) followed by sodium dithionite (38 g). The reaction was heated at reflux for 5 h, then filtered. The solid was washed with water and dried under vacuum to provide Compound 29 as a yellow solid. Yield=15 g (72.1%). ES-MS: 209.25 (M++1); NMR (DMSO-d6): δ 7.0 (m, 1H), 7.1 (m, 1H), 7.22 (m, 1H), 7.32 (m, 2H), 7.40 (m, 1H), 7.48 (m, 2H), 7.60 (m, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 5 h
  3. filtrationfiltered
  4. washThe solid was washed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f14dd1e60a094d33ba7aff9f0ba1e021
Source dataset
uspto-grants-2005_10
Patent number
US06956035B2

Reaction notes

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